5-[(3-chlorophenyl)amino]-Benzo[c]-2,6-naphthyridine-8-carboxylic acid

Base Information

• Chemical Name: 5-[(3-chlorophenyl)amino]-Benzo[c]-2,6-naphthyridine-8-carboxylic acid
• CAS No.: 1009820-21-6
• Molecular Formula: C19H12ClN3O2
• Molecular Weight: 349.77
• Hs Code.: 29339900
• Mol file: 1009820-21-6.mol

Synonyms:CX 4945;5-[(3-Chlorophenyl)amino]benzo[c]-2,6-naphthyridine-8-carboxylic acid;

Chemical Property of 5-[(3-chlorophenyl)amino]-Benzo[c]-2,6-naphthyridine-8-carboxylic acid

Chemical Property:

• Boiling Point: 568.45 °C at 760 mmHg
• PKA: 2.96±0.30(Predicted)
• Flash Point: 297.588 °C
• PSA: 75.11000
• Density: 1.491 g/cm³
• LogP: 4.95120
• Solubility.: ≥103.5 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

99% ^*data from raw suppliers

CX-4945 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: CX-4945 is a protein kinase CK2 inhibitor resulting in cancer cell death and prevention of proliferation. Anti-leukemia agent.

Technology Process of 5-[(3-chlorophenyl)amino]-Benzo[c]-2,6-naphthyridine-8-carboxylic acid

There total 5 articles about 5-[(3-chlorophenyl)amino]-Benzo[c]-2,6-naphthyridine-8-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylate → silmitasertib (1009820-21-6)

Guidance literature:

With sodium hydroxide; water; In methanol; at 50 ℃; for 0.5h;

Reference yield:

3-bromoisonicotinic acid (13959-02-9) → silmitasertib (1009820-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / Reflux

2: caesium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 100 °C / Inert atmosphere

3: trichlorophosphate / 110 °C

4: 1-methyl-pyrrolidin-2-one / 110 °C

5: sodium hydroxide / 70 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sulfuric acid; caesium carbonate; sodium hydroxide; trichlorophosphate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one;

DOI:10.1021/acs.jmedchem.1c00079

Reference yield:

ethyl 3-bromopyridine-4-carboxylate (13959-01-8) → silmitasertib (1009820-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 100 °C / Inert atmosphere

2: trichlorophosphate / 110 °C

3: 1-methyl-pyrrolidin-2-one / 110 °C

4: sodium hydroxide / 70 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; caesium carbonate; sodium hydroxide; trichlorophosphate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one;

DOI:10.1021/acs.jmedchem.1c00079

upstream raw materials:

3-bromoisonicotinic acid

ethyl 3-bromopyridine-4-carboxylate

methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate

Downstream raw materials:

5-((3-chlorophenyl)amino)-N-(2-morpholinoethyl)benzo[c][2,6]naphthyridine-8-carboxamide

Refernces

• 1、 Wang, Yuanjiang,Lv, Zhaodan,Chen, Feihong,Wang, Xing,Gou, Shaohua. "Discovery of 5-(3-Chlorophenylamino)benzo[ c][2,6]naphthyridine Derivatives as Highly Selective CK2 Inhibitors with Potent Cancer Cell Stemness Inhibition". supporting information. p. 5082 - 5098. Retrieved 2021/05/07.
• 2、 -. "SERINE-THREONINE PROTEIN KINASE AND PARP MODULATORS". Page/Page column 62-63. . Retrieved 2008/06/13.